Reacción #509102

Ecuación de reacción

methyl 2-(4-bromo-2-fluorophenylamino)-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylate

(S)-O-(2-(tert-butyldimethylsilyloxy)propyl) hydroxylamine

lithium bis(trimethylsilyl)amide

→

(S)-2-(4-Bromo-2-fluorophenylamino)-N-(2-(tert-butyldimethylsilyloxy)propoxy)-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxamide

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroat 0° C.
2. 2
   workup.ADDITIONAfter addition
3. 3
   Otroquenched by with saturated NaHCO3
4. 4
   OtroThe reaction mixture was partitioned between EtOAc
5. 5
   OtroThe layers were separated
6. 6
   Extracciónthe aqueous layer was back-extracted with EtOAc (1×)
7. 7
   SecadoThe combined organic layers were dried (Na2SO4)
8. 8
   Filtraciónfiltered
9. 9
   Concentraciónconcentrated under reduced pressure
10. 10
    Otroto yield a crude brown solid that
11. 11
    Otrowas used without further purification in the next step

Procedimiento

To a solution of methyl 2-(4-bromo-2-fluorophenylamino)-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylate (0.050 g, 0.14 mmol) and (S)-O-(2-(tert-butyldimethylsilyloxy)propyl) hydroxylamine (0.072 g, 0.35 mmol) in THF (1.50 mL) at 0° C. was slowly added lithium bis(trimethylsilyl)amide (0.70 ml, 0.70 mmol). After addition, the reaction mixture was stirred for 1 hour at room temperature and then quenched by with saturated NaHCO3. The reaction mixture was partitioned between EtOAc and sat NaCl. The layers were separated and the aqueous layer was back-extracted with EtOAc (1×). The combined organic layers were dried (Na2SO4), filtered and concentrated under reduced pressure to yield a crude brown solid that was used without further purification in the next step.

Fuente